HCID 71550224, compound → HCID 71550508, compound

HRID 925463Notes

Reaction equation

HRID 925463 reaction equation
[F:1][CH:2]([F:29])[C@@:3]1([C:10]2[CH:15]=[C:14]([NH:16][C:17]3[C:22]([O:23][CH3:24])=[CH:21][C:20]([N+:25]([O-])=O)=[CH:19][N:18]=3)[CH:13]=[CH:12][C:11]=2[F:28])[CH2:8][O:7][CH2:6][C:5]([NH2:9])=[N:4]1>CCO.[Pd]>[NH2:9][C:5]1[CH2:6][O:7][CH2:8][C@:3]([C:10]2[CH:15]=[C:14]([NH:16][C:17]3[C:22]([O:23][CH3:24])=[CH:21][C:20]([NH2:25])=[CH:19][N:18]=3)[CH:13]=[CH:12][C:11]=2[F:28])([CH:2]([F:1])[F:29])[N:4]=1

Participants

4

Reactant 1

HCID 71550224HCID 71550224, compound

Product 1

HCID 71550508HCID 71550508, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-5-difluoromethyl-5-[2-fluoro-5-(3-methoxy-5-nitro-pyridin-2-ylamino)-phenyl]-5,6-dihydro-2H-[1,4]oxazin-3-ylamine (80 mg, 0.179 mmol) in EtOH (10 ml) was added Pd—C (10%, 50 mg) the mixture was set under an atmosphere of hydrogen and stirred for 1 h. The catalyst was filtered off, the mixture diluted with DCM (20 ml) aq. sat. Na2CO3 (5 ml) was added and stirred for 5 min. The layers were separated, the aq. phase extracted with DCM (20 ml), the combined organic layers were washed with aq. sat. Na2CO3 (5 ml), dried with MgSO4 and the solvent removed under reduced pressure. The residue was purified by prep. TLC on silica gel (DCM/MeOH 9:1) to afford the title compound as purple semi-solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe mixture diluted with DCM (20 ml) aq. sat. Na2CO3 (5 ml)
  3. additionwas added
  4. stirringstirred for 5 min
  5. customThe layers were separated
  6. extractionthe aq. phase extracted with DCM (20 ml)
  7. washthe combined organic layers were washed with aq. sat. Na2CO3 (5 ml)
  8. dry with materialdried with MgSO4
  9. customthe solvent removed under reduced pressure
  10. customThe residue was purified by prep

Sources & evidence

ORD record
ord-0a6dd1b22faf4222a403f11c624ef57b
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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